Success is NOT as Simple as We Are Led to Believe

We’ve all heard the stories— a first-time entrepreneur in his 20s launches a startup online and strikes gold overnight. The media is drawn to stories of effortless success and attempting to establish a connection between youth and wisdom, where the path to riches is smooth and effortless.  But the truth is different. Many times, the greatest efforts lead to failure, or at least the final outcome is quite different from that of the original plan. This is not necessarily bad; it’s just a fact of life… And this is my three-decade story that includes several attempts at entrepreneurship, filled with valuable lessons, many derailments, weakness in perseverance, and the often-overlooked truth that God rarely gives us what we want; He gives us what provides value to His ultimate plan.

Dad’s Influence on SuperThought

As a young man, I watched my dad struggle to keep his job as an insurance salesman. After 30 years with the same company and a very successful career in sales, he was pushed out at 60 by a much younger manager.  Afterward, he bounced between jobs to support his family’s financial needs.  He died at 67 on his way to work one morning.  Witnessing his challenges, I vowed to 1) not pursue a career in sales and 2) not get caught in a similar situation as the one he experienced. Although I did not realize it then, that’s precisely where I was headed, although not intentionally, just like him. On a positive note, those feelings were instrumental in developing my interest in business ownership and freedom from a big corporate environment.  Yet, aside from the four years I invested in my first attempt at building SuperThought when I was in my early 40s, and now for the past two years, I have remained an employee for my entire career, which seemed necessary for my family’s financial security – something I did not experience as a child.

SuperThought 1.0

While at dinner one evening with my wife in 1987, I mentioned that I would like to start a technology consulting firm.  Although it was a passing comment, it slowly consumed more and more of my thoughts over the next five years.  Moving into a sales position just a year before felt unfulfilling, motivating me to look for a role that would allow me to do more than sell.  Serving as a sales rep for a big technology company did offer structure and a good income. Still, it left me feeling like I was helping the business make more money rather than serving the needs of my customers.

Thirteen more years in tech sales would pass before I was emotionally and financially ready to step out into something different. In 1997, I decided to get more serious about starting a tech business.  After almost 18 months of planning, I began organizing the components of a web design business.  One of my first steps was to secure a domain name.  Through the process of elimination, I selected superthought.com from a list of roughly 75 potential domain names.  Finally, in August 1999, I left my district sales manager position with Sun Microsystems to start SuperThought.

Much Harder Than Expected

Leaving a stable job was far more mentally challenging than I expected.  Although I believed I was stepping into a positive new chapter of my life with a sense of purpose, a fear of failure began to surface on a daily basis, which led to growing issues of self-doubt and anxiety.  The stress would not cease.  And even though the business was beginning to generate a steady income while meeting payroll requirements, the experience consumed every thought and moment of my life.

External Influence and Self-Doubt

Initially, I received praise for starting my own business, but the doubts grew louder as time passed. One particularly hurtful comment came from a friend who couldn’t understand why I would start a business so late in life at 41. The comment struck deep, reinforcing my insecurities about whether I had made a selfish choice.  This experience taught me the importance of being cautious about unsolicited input from others—a lesson I carry with me to this day.

September 11, 2001

Then, everyone’s life changed on September 11, 2001. Considering my need for stability, I saw this as a sign that it was time to make a decision focused more on my family’s needs than my aspirations. Just three months later, during the Thanksgiving weekend, I informed my wife of my plans to close the business in the near future and return to full-time employment.

Return to Employment

During the 3+ years I worked to start the business, every decision we made, every step we took, and even the successes we experienced seemed difficult.  I was hoping life would ultimately settle down when we decided to return to employment. But, once again, I was wrong.  Reentering the corporate world proved more challenging than expected due to a very soft Dot-Com market.  However, in 2003, I found stability with IBM as a Global Account Manager.

A Growing Need to Learn

As I settled into my new life with IBM, I noticed my passion for web technologies and entrepreneurship was still alive and growing.  While at SuperThought, I began taking web design courses through Indiana University for a Master’s in Media Arts, but at that time, I wasn’t confident I wanted to complete the program.  However, after several years of employment with IBM, I returned to complete the degree.  This multi-year effort stirred my interest in learning across multiple fronts.  Once I completed my Master’s in late 2008 with near-perfect grades, my desire to continue learning only accelerated.  Reaffirming my original love for technology, which started in my early twenties, I have continued my learning to this day, which includes web design and related technologies, data analytics, data management, and cloud technologies.

50% Chance of Success

Several years ago, I listened to podcast #708 from The Art of Manliness, in which the book’s author discussed the importance of a man taking on significant physical challenges where the likelihood of success is, at best, 50%. The message from this podcast connected. It helped me realize that my initial attempt to start a business was not a failure at all but an excellent growth experience. It also developed my passion for learning and pushing myself out of my comfort zone.

Beyond my professional life, I also pursued learning opportunities in other areas. As a pilot for over 30 years, I never imagined building an airplane, but by 2013, the idea began to take shape. After four years of research and talking to fellow pilots, I started a project in January 2019 to build a fabric-covered kit plane.  Five years later, I still have a long way to go.  The list of new skills I’ve had to acquire is long, including metalwork, fabric covering, painting, electrical, and much more.  And while this project has been the greatest challenge of my life, the learning opportunity and the rewards have been significant.

A Deeper Faith in Christ

Similarly, my relationship with Christ began to deepen during this time. Although I had accepted Christ in high school, my commitment was inconsistent for many years. However, the stress I encountered during those years of trying to start the business helped me realize the importance of putting Christ first in my life. This led to starting a Bible study with my sons, which has since expanded into mentoring other men and serving in church leadership.

Seven Valuable Lessons

The last 20 years have been filled with challenges but have also provided invaluable lessons. To that end, below are seven fundamental principles that have helped me grow and find peace amidst the difficulties of life:

1. Build a Relationship with Jesus Christ—I believe a life without Jesus Christ is not worth living. As I have invested more and more time studying the Bible and learning the truth about God’s love and grace, I have realized that peace and contentment are impossible without Him. If you need more confidence in this yourself, please send me a note.
2. Prioritize Your Family—This one is obvious. Still, entrepreneurs are often so focused on building the business that their family suffers. Don’t let yourself become consumed.
3. Learn to Be Patient—Patience is crucial to business success. My experience in sales conditioned me to think of short-term gains, but building a business requires a long-term focus and the ability to endure delays and setbacks.
4. Invest in Your Personal Growth – Invest in your knowledge and skills before starting a business. I realize now that I was unprepared when I started SuperThought. Continuous learning is vital to success.
5. Be Cautious of Unsolicited Input from Others – Seek guidance from those you trust and respect, but be selective about the advice you take. Not all input is beneficial.
6. Surround Yourself with Trusted Allies—Surround yourself with people you trust and who will provide needed accountability. Share your concerns and worries with trusted allies to avoid bringing those feelings home to your spouse.
7. Reward Yourself for Small Accomplishments—Many months can easily pass without you ever experiencing success. So, you must find ways to identify and celebrate even the smallest accomplishments.

Turning Pain into Purpose

The past two decades have also brought pain, including two layoffs that left me questioning my direction and purpose. But I’ve chosen to use these experiences to define rather than destroy me. As a result of those experiences, I’m pursuing ways to help others transition from corporate environments to entrepreneurship or rebuild their lives after a layoff.

SuperThought 2.0 – Life Today

While SuperThought is different today than in 1999, what’s changed the most is me. And needless to say, I’m at a completely different stage of life than I was 25 years ago. But more importantly, my views on life and business have changed significantly. Today, my primary business goal is to help small tech firms become more successful via quality website design and related services that will allow the owner to focus on his/her top priority, selling to and supporting their clients. 

Looking back, I realize that while working in Big Tech has its perks, my true calling lies in entrepreneurship. It allows me the autonomy, flexibility, and control I’ve always desired. The journey has been far from easy but richly rewarding, filled with lessons that continue to shape who I am today. Success is not as simple as we’re often led to believe—but it’s worth every challenge when you stay true to your values and long-term goals.

The Most Important Lesson

Through it all, I’ve begun to understand that while I carefully developed my plans and prayed many times for God to bless them, God’s purpose, not mine, was ultimately unfolding in ways I couldn’t yet see. The challenges, doubts, and constant worry were part of a bigger story that wasn’t just about business success but about learning to trust that His plans would prevail—even when my own were unclear. This realization has become a source of strength as I navigate the uncertainties today. They remind me that true peace doesn’t come from external success but from aligning with God’s purpose—His will, Not Mine.